


Many Midnight Shenanigans.

by exiledOptimism



Category: Homestuck, Mobsterswitch - Fandom, Problem Sleuth (Webcomic)
Genre: Bawd's eyes, Candy Corn Vampire costumes, Christmas, Club Twilight, Crossdressing, Expect plenty of holiday stuff in here, F/F, F/M, Fainting, Fear, Halloween, Haloween parties, Human AU, Is chapter three legal?, Language, Lecturing, M/M, Mention of Scofflaw's death, Midnight Crew - Freeform, Mobsterswitch, Please tell me this is a thing that I can do., Shy Violet by Owl City, Suits, Tea, Team Sleuth, hhh - Freeform, yep
Language: English
Status: In-Progress
Published: 2015-08-28
Updated: 2016-05-23
Packaged: 2018-04-17 17:24:22
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 16
Words: 2,836
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4675112
Author URL: https://archiveofourown.org/users/exiledOptimism/pseuds/exiledOptimism
Summary: <blockquote class="userstuff">
              <p>A series of shorts, shipping snippets written at school.</p>
            </blockquote>





	1. Date Night

**Summary for the Chapter:**

> Diamonds Droog doesn't know what Pickle Inspector is wearing, but it looks okay.

You aren't sure what to call him tonight. You told Slick you were meeting about an information exchange, even if that wasn't true. It was a dinner date. When you arrived, he was already there.

He was stirring his tea, humming to himself. So very peaceful. When he looked at you, he smiled and stood up. He made his way over, grinning from ear to ear in his gorgeous way. He was wearing black though.

He led you to the table and waved a waitress over. You ordered coffee, pure damn black. He gave you a nasty look when you cursed and after the waitress abandoned you, he brought it up. You shouldn't use such language on such a formal date, he scolded, it was improper etiquette.

You discussed this for a short amount of time before you brought up the suit. He told you he rented it just for this date. You were honored.

You so love him so.


	2. Happy Halloween!

**Summary for the Chapter:**

> Problem Sleuth supposes it didn't hit worst until they showed up.

**Notes for the Chapter:**

> No, it isn't too early for this. I swear.

You were hardly surprised when the Midnight Crew invited themselves to your team's party. Probably an idea of Slick's. You weren't too bothered until it came to your mind that hey.

These idiots are out of costume.

You directed them to refreshments anyway, disregarding it. You'd ask one of them about it later.

After a while of mulling around, you assume Slick got bored. He decided to bother you, asking what you are.

You told him that you were a vampire and asked him what he was.

He's himself, dumbass. What else would he be?

That made you sigh.

Yeah, he is, you tell him. He's a shit Spades Slick too. You kissed his cheek and decided you should busy yourself. You had a party to tend to.


	3. Fear

**Summary for the Chapter:**

> Pickle Inspector is pretty sure that Ace Dick put that paper bat in his closet.

**Notes for the Chapter:**

> Is this a thing that I can actually do? I hope so.

You needed a mop to clean up some tea that someone knocked off your desk. You were that someone. Thankfully, though, it was only tea and could be cleaned up easily. As you headed for the supply closet, you were aware that Ace Dick was watching you. He was waiting for something and you knew it.

You opened the door with an absentminded hum.

Of course, it cut into a screech when a black figure dropped in front of your face.

* * *

 

You guess you fainted. You probably fainted. This is your assumption, because when your eyes opened, green eyes were gazing into yours with distinct concern and Problem Sleuth's arms wrapped around you.

You suppose fear can work wonders, because you were able to muster up the courage to wrap your arms around him.

**Notes for the Chapter:**

> Yeah. It is.


	4. Shy Violet Angel Eyes

**Summary for the Chapter:**

> Heinous Doxy liked those eyes, and that woman.

**Notes for the Chapter:**

> Please don't try to stop me.

She'd smile and compliment you whenever you finished a performance. You didn't mind, even when they changed from your choice of songs to your outfit and even if she was with Innovator, it made you want to wrap her up and sing to those shy violet eyes.

Since Scofflaw's...Death? Destruction? Whatever. Since his whatever, you'd been kind of leaning on her.

While Inny was in the office of Club Twilight, she was helping you prepare to call it a night. She was such an angel.

She smiled at you and yeah, you know what you saw and you knew what drew Innovator to her.

The warmth in those shy violet angel eyes.


	5. Merry Christmas, Spades Slick!

**Summary for the Chapter:**

> Clubs Deuce thinks that maybe Snowman was making a joke when she left Slick his "present."

**Notes for the Chapter:**

> I know it's too early for this, but what can I do? Stop? No.

You loved this holiday. Not as much as Halloween, but you loved it. Presents and all. You aren't sure why Slick invited Sleuth and his buddies over, but you aren't about to complain. The more the merrier.

You guys all did a secret Santa thing. You got Boxcars candy, even if you weren't supposed to tell him that. Someone got Droog a tie (totally that Pickle guy), and you think that Droog got him a real pretty choker. Someone got you TNT, Slick got licorice scottie dogs, Sleuth got a lot of candy corn, and Ace got a mug that said DICK in big letters. Snowman even brought Slick something! A jar with... His eye...

That made him pretty angry.

You listened to him curse with Boxcars next to you, watching Droog help Inspector put the choker on while Sleuth stuffed his face with candy corn and Dick napped on the table. You had no problem with that.

When Slick finally calmed down, Sleuth grinned a real snarky grin.

"Merry Christmas, Spades Slick."


	6. She's sporting what?

**Summary for the Chapter:**

> Problem Sleuth didn't think Nervous Broad was serious when she said Dame was strutting around in one of his suits. How wrong he was.

When Broad told you, you had one question. "She's sporting... What?"

"She's borrowed one of your suits." That made you laugh.

The thing was, she was serious. You ran into Dame later on, not so much on accident, and she really was sporting one of your suits.

How did she even get her paws on that?

Man, it looked good though, with her orchid eyes that blinked in recognition.

"Sleuth," she greeted, striking a pose.

"Dame. Lookin' good."

"You know, now you gotta wear one of my dresses somewhere."

"...When?" 

"Tonight. Casino." She grinned.

"Deal." You decided you'd have her do your hair to look like her too. Oh, this would be all kinds of fun.


	7. Size

**Summary for the Chapter:**

> Wow, Pickle Inspector didn't realize just how tall he really was.

**Notes for the Chapter:**

> Based off an rp with the wonderful Rei!

When you go to get groceries too late, bad things happen. Going to the store at Midnight on Midnight Crew territory was a horrid idea.

You didn't act as mortified as you were when Spades Slick started casing you or pulled you into an alleyway on your way to the post office and ordered you to show him where your home was. You knew better than to let him know that you might have a heart attack.

You kept your mouth shut about that letter and the way he had to reach up to hold onto your collar and shove you forward, and about how much effort he put into it.

Despite the switchblade in his hand, it was pretty humorous. You had to suppress your laughter, watching the little mob boss jog along every few paces. 

He was panting by the time you both arrived at your apartment complex. It was all you could do to be polite and pretend that you weren't amused.

You couldn't wait to see him try to get up the five flights of stairs.

He slipped away his switchblade and released your collar, starting his run up those stairs.

You kept trailing behind, laughing quietly. You didn't have a death wish.

When he wore himself out at the second story, you stopped with him. Godhead have mercy.

You had to say, it was pretty great being tall and watching these shorties.


	8. Days at a Time

**Summary for the Chapter:**

> Unlike the rest of the city, Problem Sleuth doesn't always have to live day-by-day. He does so by choice lately.

**Notes for the Chapter:**

> I'm sorry?

Living in Midnight City can teach a guy how to take it step by step. Working against the Midnight Crew can teach a guy how to live day by day, make minimum plans for tomorrow.

Having a "thing" with Spades Slick can teach a guy how to watch his back.

It can also teach a guy how to tell the approximate time without a clock. He really hated those things.

Now, your "thing" with Spades Slick was what drew you to stay up way too late, to slip into the back door of his Casino and pretend that it wasn't a bad idea.

It pushed you to follow him to a back room to share a bottle of whiskey and have sex.

He kept you moving. He moved days at a time, and that wasn't your style. Even if your "thing" with Spades Slick allowed you to do such a thing.

You moved day by day.

You loved it too.


	9. Gentle

**Summary for the Chapter:**

> Diamonds Droog is rarely a gentle man, but there are times when he can be.

You'd thread your fingers through Pickle Inspector's fluffy blonde hair and he'd smile. You'd smile back, the smallest of smiles, and you knew that he'd notice. That made you happy.

He'd curl up to you and he knew that he saw something that nobody else did.

He knew that you were gentle for him.

He'd cling to you for dear life, crystal blue eyes closing as you continued to play with his hair.

You wanted to do something with that hair some day.

He was beautiful, no matter his pulchritude level or his own thoughts. You knew that Pickle Inspector was worth being gentle.


	10. Team

**Summary for the Chapter:**

> Problem Sleuth endures a lot of pain from the city, but he has his team.

Sometimes, the city hurt. Well, it hurt you. You got used to it after a while, the dirty looks and elbowing from mobsters that crossed your path.

You got used to them removing files from your hands, just like older kids would in school.

You tried being nice, and it failed. You tried fighting back, and it failed. Everything failed.

The city hurt.

You still smiled, though, because you had your shootouts and booze and your team.

You had your team and that made all of it worth enduring. So, you threw an arm around a plastered Ace Dick and dragged Pickle Inspector closer.

You had your team and you know what? Everyone else could go fuck themselves.


	11. Christmas Shopping

**Summary for the Chapter:**

> Diamonds Droog hates holidays, but watching a particular two detectives shop gives him a little insight into what makes them so cheery.

**Notes for the Chapter:**

> So, I've been really inactive lately, I know. With Christmas drawing nearer, though, I wanted to go ahead and update this one before I start typing up stuff that I've got on paper in this series.

You didn't understand Christmas. The ridiculous sweaters, the bright lights, and the kids. You didn't get why people were so happy. The smell of cinnamon annoyed you and so did Christmas tunes.

 

That said, you didn't understand what made Pickle Inspector so happy. He'd insisted that he had things to do and slipped off and you, unbeknownst to him, followed. He met up with Problem Sleuth, who grinned up at him. 

 

Inspector smiled back and the two talked in hushed tones. It annoyed you that you couldn't hear what they were speaking of. The pair entered a thrift store, and Sleuth came out with a stocking. A big, fuzzy, useless sock. You didn't understand why. Inspector had one too, when he exited, but in red rather than green.

 

"Y'know," Sleuth commented, "I don't think that Slick is gonna like this thing.He'll like what's in it though."

"I'm certain that Mister Droog will enjoy his," Inspector responded. "A Christmas present is a Christmas present after all."

 

Shit. Christmas presents. You had yet to even think about his. 

 

Oh well, you'd find something. A Christmas present is a Christmas present and the holidays are about giving. Even if it was only a good fuck that was given.

**Notes for the Chapter:**

> Okay, maybe it's not so good. Whatever.


	12. Getting Somewhere

**Summary for the Chapter:**

> Peccant Scofflaw is the leader of this team and gets each member somewhere, even if just to sleep.

You lied. A lot. You  _knew_ that you lied a lot too. But what could you do? After all, you were only sort of human. Extra emphasis on _sort of._ You guessed that shadow magic made you kind of not quite human. Gazing upon Pernicious Innovator made you realize just how often you lied to him.

 

But hey, you weren't human. You felt no remorse whatsoever. Why would you feel  _remorse_?

 

You looked upon the other three that you shared the table with. You were their leader, you had to keep this team strong even if it meant lying to them.

 

Especially to  _him._ Otherwise you'd get nowhere. You needed to get somewhere. 

 

Angry Delinquent had fallen asleep with his head on the table and you could only sigh. He was asleep and he was asleep. That was your full opinion. You couldn't do anything but wake him up to fix it, and you didn't feel like waking him up. You looked at Bawd, chatting quietly with Innovator. You smiled a little before you looked at Doxy. She was yours. Your Heinous Doxy. 

 

She was seated next to you and seemed a bit confused when you wrapped your arm around her. After a moment, she cuddled into your side, comfortable in her seat. You see it in her eyes, she was tired. You ran a gentle hand through her black hair as an encouragement for her to go on to sleep.

 

She looked up at you and kissed your cheek before murmuring that she wanted you to sing to her. You gave her a look. You? Sing? In front of Innovator? And Bawd? Was she serious?

 

She was. You gave in with a sigh before you began singing.

 

 _"I went to a garden party to reminisce with my old friends._  
A chance to share old memories and play our songs again.  
When I got to the garden party, they all knew my name  
But no one recognized me, I didn’t look the same.

 

_"But it’s all right now, I learned my lesson well.  
You see, you can’t please everyone so you gotta please yourself."_

 

You looked at her. She had her eyes closed. She wasn't asleep, but she was pretending to be. You grinned and kissed her forehead before looking up at Bawd and Innovator. They looked away and you couldn't help but sigh.

 

Whatever. You were the leader of this team and you were gonna get them somewhere, even if it meant just getting your girlfriend to sleep.


	13. Pain

**Summary for the Chapter:**

> Sometimes, the city hurts Problem Sleuth. Though, he can cope.

**Notes for the Chapter:**

> I wrote this forever ago so here. The page literally says chapter ???

Sometimes, the city hurt. Well, it hurt you. You got used to that feeling after a while, being elbowed by whomever didn't like you when they asked near. That said, a lot of people didn't like you. They'd push files out of your hands and all. 

 

Fights only made things worse, pulchritude made you seen vain. Nothing worked. 

 

The city hurt. 

 

You still smiled though. You smiled every day, every night. You smiled because you had your spirits and you had alcohol, but best of all, you had your team. Yeah. 

 

You had your team and that was pleasing. You proceeding to throw an arm around Ace Dick before dragging Pickle Inspector nearer. You had your team. 

 

Everyone else could go fuck themselves. 


	14. Taking a Break

He didn't fight back. He never did. Sometimes, it pissed you off but other times, you guessed it was for the best.

 

You guess he thought the same, so he never intentionally started a fight with you outside of work. He popped up in your apartment on fucking Thursday sometimes, stepping up behind you as you read the news. Today, he has those gangly hands rubbing your shoulders while you ranted about your day. You guessed that you were enjoying it, even if you hated him. It was nice to do this kind of thing.

 

"You know, he's beyond stupid to believe that I'd  _ever_ risk my safety over a damn knife. Finances might be tough right now, but that doesn't mean that one knife is that important. I don't understand who he thinks he is. He's my boss, yeah. He signs my paycheck, but I'm still more his babysitter than anything," you said. Innovator nodded, hands rubbing down over your chest. 

 

"You know, Detective, it sounds to me like you deserve to take a break and rest up," he commented. You guessed that it was that obvious that you were wearing thin.

 

"Yes, I agree. Perhaps you do as well, Innovator. You've been beat black and blue countless times yet you've never once spoken a word of complaint to me." You looked up at the man, who's hands never stopped moving. 

 

"Of course not. I have nothing to complain about."

 

He sounded nuts to you. His boss beat him, his enemies beat him,  _you_ beat him. He never stopped getting hurt, and yet, there he was. Rather than resting or eating (he could use a meal, the man was to thin to be eating enough), he was standing there and listening to you bitch. Not just listening, he was trying to help you relax. Not feeding himself or anything of the like, he was  _massaging your goddamn shoulders and listening to you complain._

 

You sighed. "You have more than a reason to complain. You deal with far too much. If I deserve a break, you deserve much more of one. Are you hungry?"

 

He shook his head, smiling. "No, dear. I should be going though."

 

"Must you?"

 

"I'm afraid. But do me a favor, if you are willing to take a break and stay from work tomorrow, I'll visit."

 

"Alright."

 

And he vanished. Teleported out. You sighed. 

 

Looked like you were taking a break tomorrow. 


	15. Maybe

**Summary for the Chapter:**

> Pernicious Innovator needs to stop thinking.

_"Madmen know nothing..."_

_Edgar Allan Poe; A Telltale Heart_

 

You think back to a quote that you know very well. You don't think it's true. Either that, or the gang wasn't mad. 

 

Maybe they aren't insane. 

 

Maybe your souls would rest in peace. 

 

Maybe your relationship with Bawd was okay. 

 

Maybe she wasn't flirting with Doxy and it was all in your mind. 

 

Maybe... 

 

Maybe you should stop thinking on the subject. 

 

Maybe you should stop thinking at all for your own good. 

 


	17. It's Fine

**Summary for the Chapter:**

> Even when he cries, there is no doubt that Problem Sleuth is one of the strongest and luckiest men in the city. Especially with his team and the two lovely lady friends of theirs behind them.

**Notes for the Chapter:**

> This one looks way pointless to me but I really like the concept behind it so here.

For the sake of the warm hands that held his when he cried, Problem Sleuth didn't hold back the tears. Even the strongest got scared, right?

 

Right. Dame said so and she was holding his hand. She was helping.

 

Even with Inspector M. I. A., she was there.

 

Even with tears running down his cheeks, someone was there for him. That made him feel like the luckiest man in the city. They'd find Inspector, he knew it. It was just the Crew, he was fine.

 

He would be fine soon.

 

And when those warm hands let go of his and wiped his cheeks, Problem Sleuth grinned. For a detective whose income wasn't enough to meet the standards of a woman continuing the legacy of a brothel, he was sure that Dame was there to help. He was positive.

 

Problem Sleuth grinned from ear to ear as he made eye contact with Hysterical Dame. Everything was fine.


End file.
